SK6002000A3 - A process for the preparation of chiral imidazolinone herbicides - Google Patents

A process for the preparation of chiral imidazolinone herbicides Download PDF

Info

Publication number: SK6002000A3
Authority: SK; Slovakia
Prior art keywords: acid; formula; methyl; oxo; isopropyl
Prior art date: 1999-05-03

Application number

SK600-2000A

Other languages

English (en)

Slovak (sk)

Inventor

Thomas Walter Drabb

Peter John Wepplo

Original Assignee

American Cyanamid Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1999-05-03

Filing date

2000-04-26

Publication date

2000-12-11

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=23174474&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=SK6002000(A3) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2000-04-26 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

2000-12-11 Publication of SK6002000A3 publication Critical patent/SK6002000A3/sk

Links

238000000034 method Methods 0.000 title claims abstract description 29
238000002360 preparation method Methods 0.000 title claims abstract description 11
CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 title abstract description 13
239000004009 herbicide Substances 0.000 title abstract description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 23
239000002585 base Substances 0.000 claims description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 11
239000002904 solvent Substances 0.000 claims description 11
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 7
-1 alkali metal alkoxide Chemical class 0.000 claims description 7
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 7
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical group [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 7
229910052783 alkali metal Inorganic materials 0.000 claims description 5
150000005690 diesters Chemical class 0.000 claims description 5
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
CUGUEZKINWGNPZ-LURJTMIESA-N (2R)-2,3-dimethylbutane-1,2-diamine Chemical compound CC(C)[C@@](C)(N)CN CUGUEZKINWGNPZ-LURJTMIESA-N 0.000 claims description 3
NUPJIGQFXCQJBK-OAHLLOKOSA-N (R)-imazamox Chemical compound OC(=O)C1=CC(COC)=CN=C1C1=N[C@](C)(C(C)C)C(=O)N1 NUPJIGQFXCQJBK-OAHLLOKOSA-N 0.000 claims description 3
239000011260 aqueous acid Substances 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
PVSGXWMWNRGTKE-CQSZACIVSA-N (R)-imazapic Chemical compound N1C(=O)[C@](C(C)C)(C)N=C1C1=NC=C(C)C=C1C(O)=O PVSGXWMWNRGTKE-CQSZACIVSA-N 0.000 claims description 2
XVOKUMIPKHGGTN-OAHLLOKOSA-N 5-ethyl-2-[(4r)-4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl]pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC(CC)=CN=C1C1=N[C@](C)(C(C)C)C(=O)N1 XVOKUMIPKHGGTN-OAHLLOKOSA-N 0.000 claims description 2
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
150000002170 ethers Chemical class 0.000 claims description 2
150000008282 halocarbons Chemical class 0.000 claims description 2
229930195733 hydrocarbon Natural products 0.000 claims description 2
150000002430 hydrocarbons Chemical class 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
CABMTIJINOIHOD-QGZVFWFLSA-N (R)-imazaquin Chemical compound N1C(=O)[C@](C(C)C)(C)N=C1C1=NC2=CC=CC=C2C=C1C(O)=O CABMTIJINOIHOD-QGZVFWFLSA-N 0.000 claims 1
DCKOJKCSWDKXIF-UHFFFAOYSA-N 4-methyl-4-propan-2-yl-1h-imidazol-5-one Chemical compound CC(C)C1(C)N=CNC1=O DCKOJKCSWDKXIF-UHFFFAOYSA-N 0.000 claims 1
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 1
239000003513 alkali Substances 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
229910052751 metal Inorganic materials 0.000 claims 1
239000002184 metal Substances 0.000 claims 1
235000001968 nicotinic acid Nutrition 0.000 claims 1
239000011664 nicotinic acid Substances 0.000 claims 1
125000003944 tolyl group Chemical group 0.000 claims 1
YCPQUHCGFDFLSI-ZCFIWIBFSA-N (2r)-2-amino-2,3-dimethylbutanamide Chemical compound CC(C)[C@@](C)(N)C(N)=O YCPQUHCGFDFLSI-ZCFIWIBFSA-N 0.000 abstract description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
239000000047 product Substances 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
230000002363 herbicidal effect Effects 0.000 description 4
239000000203 mixture Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000000605 extraction Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
230000014759 maintenance of location Effects 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
239000012071 phase Substances 0.000 description 2
238000010966 qNMR Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
239000000243 solution Substances 0.000 description 2
YCPQUHCGFDFLSI-LURJTMIESA-N (2s)-2-amino-2,3-dimethylbutanamide Chemical compound CC(C)[C@](C)(N)C(N)=O YCPQUHCGFDFLSI-LURJTMIESA-N 0.000 description 1
CLQMBPJKHLGMQK-CYBMUJFWSA-N (R)-imazapyr Chemical compound N1C(=O)[C@](C(C)C)(C)N=C1C1=NC=CC=C1C(O)=O CLQMBPJKHLGMQK-CYBMUJFWSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
YCPQUHCGFDFLSI-UHFFFAOYSA-N 2-amino-2,3-dimethylbutanamide Chemical class CC(C)C(C)(N)C(N)=O YCPQUHCGFDFLSI-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
150000004816 dichlorobenzenes Chemical class 0.000 description 1
ZCDHDTQWOJRFFE-UHFFFAOYSA-N dimethyl 5-(methoxymethyl)pyridine-2,3-dicarboxylate Chemical compound COCC1=CN=C(C(=O)OC)C(C(=O)OC)=C1 ZCDHDTQWOJRFFE-UHFFFAOYSA-N 0.000 description 1
MKOJTLPEGLTEFM-UHFFFAOYSA-N dimethyl 5-methylpyridine-2,3-dicarboxylate Chemical compound COC(=O)C1=CC(C)=CN=C1C(=O)OC MKOJTLPEGLTEFM-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
229940017219 methyl propionate Drugs 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 description 1
GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical class OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/06—Nitrogen directly attached to an aromatic ring system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (AREA)
General Health & Medical Sciences (AREA)
Pest Control & Pesticides (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pyridine Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

SK600-2000A 1999-05-03 2000-04-26 A process for the preparation of chiral imidazolinone herbicides SK6002000A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US09/303,967 US5973154A (en)	1999-05-03	1999-05-03	Process for the preparation of chiral imidazolinone herbicides

Publications (1)

Publication Number	Publication Date
SK6002000A3 true SK6002000A3 (en)	2000-12-11

Family

ID=23174474

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK600-2000A SK6002000A3 (en)	1999-05-03	2000-04-26	A process for the preparation of chiral imidazolinone herbicides

Country Status (18)

Country	Link
US (1)	US5973154A (fr)
EP (1)	EP1050533A1 (fr)
JP (1)	JP2000319276A (fr)
KR (1)	KR20010029680A (fr)
CN (1)	CN1272496A (fr)
AR (1)	AR025522A1 (fr)
AU (1)	AU3024300A (fr)
BR (1)	BR0002073A (fr)
CA (1)	CA2307391C (fr)
HU (1)	HUP0001710A3 (fr)
IL (1)	IL135795A (fr)
IN (1)	IN187740B (fr)
MX (1)	MXPA00004111A (fr)
NZ (1)	NZ504204A (fr)
PL (1)	PL339971A1 (fr)
SK (1)	SK6002000A3 (fr)
TW (1)	TWI223650B (fr)
ZA (1)	ZA200002131B (fr)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
PT2272350E (pt)	2004-04-01	2013-04-10	Basf Agrochemical Products Bv	Misturas herbicidas que atuam de forma sinergética
KR20080081979A (ko) *	2005-12-23	2008-09-10	바스프 에스이	수생 잡초의 억제 방법
AU2006328476A1 (en) *	2005-12-23	2007-06-28	Basf Se	A method of controlling the aquatic weed Hydrilla verticillata
US9210930B2 (en) *	2005-12-23	2015-12-15	Basf Se	Control of submerged aquatic vegetation
US20090176648A1 (en) *	2006-04-07	2009-07-09	Thomas Byrne	Herbicidal Mixture, Comprising an Imidazolinone Herbicide and an Adjuvant
DK2296466T3 (da)	2008-06-18	2014-06-16	Basf Se	Ternære herbicidale sammensætninger, der omfatter aminopyralid og imazamox
WO2010055042A1 (fr) *	2008-11-13	2010-05-20	Basf Se	Acides 2-[(1-cyanopropyl)carbamoyl]-5-méthoxyméthylnicotiniques et leur emploi dans la fabrication d'imidazolidones herbicides
CN102245578B (zh) *	2008-11-13	2015-01-07	巴斯夫欧洲公司	制备5-氯甲基-2,3-吡啶二甲酸酐的方法
CN102245577B (zh) *	2008-11-13	2014-03-26	巴斯夫欧洲公司	2-[(1-氰基丙基)氨基甲酰基]-5-氯甲基烟酸及其在制备除草咪唑啉酮中的用途
WO2010132873A2 (fr)	2009-05-15	2010-11-18	Northwestern University	Composés à noyau pyrrolidine chiraux utilisés pour la préparation d'inhibiteurs d'oxyde nitrique synthase
BR112013003029A2 (pt)	2010-08-24	2016-09-13	Basf Se	mistura agroquímica, composição agroquímica, método para aumentar sinergicamente a saúde de uma planta e usos de uma mistura
IN2014CN04928A (fr)	2011-12-05	2015-09-18	Basf Agrochemical Products Bv
CA3044164A1 (fr)	2016-11-21	2018-05-24	Adama Agan Ltd.	Procede de preparation de methoxy methyl pyridine dicarboxylate
EA202191587A1 (ru)	2018-12-18	2021-10-20	Басф Агрокемикэл Продактс Б.В.	Гербицидные комбинации
EA202191586A1 (ru)	2018-12-18	2021-10-19	Басф Агрокемикэл Продактс Б.В.	Гербицидная композиция
EP3897137B1 (fr)	2018-12-18	2025-07-30	BASF Agrochemical Products B.V.	Combinaisons herbicides
WO2020126583A1 (fr)	2018-12-18	2020-06-25	Basf Agrochemical Products B.V.	Combinaisons herbicides
EP3897141A1 (fr)	2018-12-18	2021-10-27	BASF Agrochemical Products B.V.	Combinaisons herbicides
WO2020126582A1 (fr)	2018-12-18	2020-06-25	Basf Agrochemical Products B.V.	Combinaisons herbicides
RU2707043C1 (ru) *	2019-03-25	2019-11-21	Акционерное общество "Щелково Агрохим"	Способ получения гербицида имазамокса
CN113061125B (zh) *	2019-12-13	2022-11-01	沈阳中化农药化工研发有限公司	一种咪唑啉酮化合物的制备方法
CN113620928A (zh) *	2021-08-16	2021-11-09	辽宁先达农业科学有限公司	一种甲氧咪草烟钠盐的合成方法
AR127168A1 (es)	2021-09-28	2023-12-27	Basf Agrochemical Products Bv	Imazamox y glifosato para controlar digitaria insularis

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4683324A (en) *	1982-05-25	1987-07-28	American Cyanamid Company	Process for the resolution of certain racemic amino nitriles
ATE43845T1 (de) *	1983-06-02	1989-06-15	American Cyanamid Co	(2-imidazolin-2-yl)thieno-und furo(2,3-b)-und (3,2-b)-pyridine und zwischenprodukte, ihre herstellung und ihre verwendung als herbizide mittel.
ES2043685T3 (es) *	1986-02-10	1994-01-01	Ciba Geigy Ag	Procedimiento para la preparacion de acidos 2-(imidazolin-2-il)piridin- y quinolin-3-carboxilicos.
EP0296109A3 (fr) *	1987-06-18	1989-12-20	Ciba-Geigy Ag	Dérivés de l'acide nicotinique -2(imidazolin-2-yl)
US4925944A (en) *	1989-03-21	1990-05-15	American Cyanamid Company	Process for the preparation of o-carboxypyridyl- and o-carboxyquinolylimidazolinones

1999
- 1999-05-03 US US09/303,967 patent/US5973154A/en not_active Expired - Fee Related
2000
- 2000-04-24 IL IL13579500A patent/IL135795A/en active IP Right Grant
- 2000-04-25 JP JP2000123949A patent/JP2000319276A/ja not_active Withdrawn
- 2000-04-26 SK SK600-2000A patent/SK6002000A3/sk unknown
- 2000-04-27 NZ NZ504204A patent/NZ504204A/en unknown
- 2000-04-27 CN CN00108177A patent/CN1272496A/zh active Pending
- 2000-04-27 MX MXPA00004111A patent/MXPA00004111A/es unknown
- 2000-04-28 PL PL00339971A patent/PL339971A1/xx not_active Application Discontinuation
- 2000-04-28 EP EP00303585A patent/EP1050533A1/fr not_active Ceased
- 2000-05-01 KR KR1020000023246A patent/KR20010029680A/ko not_active Ceased
- 2000-05-01 IN IN257CA2000 patent/IN187740B/en unknown
- 2000-05-01 CA CA002307391A patent/CA2307391C/fr not_active Expired - Fee Related
- 2000-05-02 AR ARP000102094A patent/AR025522A1/es unknown
- 2000-05-02 HU HU0001710A patent/HUP0001710A3/hu unknown
- 2000-05-02 TW TW089108313A patent/TWI223650B/zh not_active IP Right Cessation
- 2000-05-02 ZA ZA200002131A patent/ZA200002131B/xx unknown
- 2000-05-02 AU AU30243/00A patent/AU3024300A/en not_active Abandoned
- 2000-05-02 BR BR0002073-7A patent/BR0002073A/pt not_active Application Discontinuation

Also Published As

Publication number	Publication date
HU0001710D0 (en)	2000-06-28
IL135795A (en)	2004-05-12
US5973154A (en)	1999-10-26
TWI223650B (en)	2004-11-11
NZ504204A (en)	2001-09-28
CA2307391A1 (fr)	2000-11-03
IN187740B (fr)	2002-06-15
JP2000319276A (ja)	2000-11-21
EP1050533A1 (fr)	2000-11-08
AR025522A1 (es)	2002-12-04
BR0002073A (pt)	2001-01-02
KR20010029680A (ko)	2001-04-06
AU3024300A (en)	2000-11-09
IL135795A0 (en)	2001-05-20
ZA200002131B (en)	2000-11-07
HUP0001710A2 (hu)	2001-05-28
CA2307391C (fr)	2008-07-08
MXPA00004111A (es)	2002-07-22
PL339971A1 (en)	2000-11-06
CN1272496A (zh)	2000-11-08
HUP0001710A3 (en)	2002-12-28

Publication	Publication Date	Title
SK6002000A3 (en)	2000-12-11	A process for the preparation of chiral imidazolinone herbicides
US6339158B1 (en)	2002-01-15	Process for the preparation of chiral nicotinic, quinolinic or benzoic acid imidazolinone herbicides
JP3120873B2 (ja)	2000-12-25	ピリジン誘導体
EP0470795A1 (fr)	1992-02-12	Procédé pour la préparation de nitriles
US4758667A (en)	1988-07-19	Process for the preparation of 2-(imidazolin-2-yl)-3-pyridine- and -3-quinolinecarboxylic acids
CN113061125A (zh)	2021-07-02	一种咪唑啉酮化合物的制备方法
EP0205879B1 (fr)	1993-03-17	Procédé de préparation d'acides herbicides 2-(4,4-disubstitué-5-oxo-2-imidazolin-2-yl)benzoiques, nicotiniques et quinoline-3-carboxyliques, de leurs esters et de leurs sels
EP0144595B1 (fr)	1989-01-18	Préparation d'acides carbamoyl-2 nicotiniques et quinoléine-car-boxyliques-3
EP0095105B1 (fr)	1988-01-27	Procédé de préparation d'acides 2-(4-oxo-2-imidazolin-2-yl-5,5-disubstitué)nicotinique, -quinoline-3-carboxylique et benzoique
CZ72193A3 (en)	1994-01-19	Biphenylmethyl substituted pyridones
MXPA05003994A (es)	2005-06-22	Metodo para la sintesis de un compuesto de bencimidazol.
EP0325730B1 (fr)	1994-06-15	Procédé de préparation de O-carboxyarylimidazolinones
EP0968204A1 (fr)	2000-01-05	Procede de preparation de 2- 2-pyridinyl)methyl]sulfynyl]-1h-benzimidazoles et nouveaux composes a utiliser dans ledit procede
KR930001408B1 (ko)	1993-02-27	치환 및 비치환 2-카르바모일 니코틴산 및 3-퀴놀린 카르복실산의 제조방법
EP0142718B1 (fr)	1987-03-11	Préparation d'acides [(carbamoyl-1 diméthyl-1,2 propyl)carbamoyl]-2 quinoléinecarboxyliques-3, nicotiniques et benzoiques substitués et non substitués
KR20230026411A (ko)	2023-02-24	방향족 에터 화합물의 제조 방법
US4925944A (en)	1990-05-15	Process for the preparation of o-carboxypyridyl- and o-carboxyquinolylimidazolinones
CZ20001607A3 (cs)	2000-12-13	Způsob přípravy chirálních imidazolinonových herbicidů
CA2208129C (fr)	2007-01-02	Procede pour la preparation (4-aryl-2,5-dioxoimidazo-lidin-1-yl) acide acetique chiral et non-racemique
KR900003391B1 (ko)	1990-05-18	2-(5,5-디치환-4-옥소-2-이미다졸린-2-일)니코틴산 및 퀴놀린-3-카복실산류의 제법
US4959476A (en)	1990-09-25	Method for the preparation of herbicidal O-carboxyarylimidazolinones
EP1019376A1 (fr)	2000-07-19	Derives de pyridone, leur preparation et leur utilisation comme intermediaires de synthese
US5103009A (en)	1992-04-07	Method for the preparation of herbicidal intermediates
US5034532A (en)	1991-07-23	Method for the preparation of quinolyl and pyridyl substituted imidazolinones
CZ146596A3 (en)	1997-01-15	Substituted quinolines as herbicidal intermediates and process for preparing thereof